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https://doi.org/10.5562/cca2482

Photodecarboxylation of N-Adamantyl- and N-Phenylphthalimide Dipeptide Derivatives

Margareta Sohora ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička 54, 10000 Zagreb, Croatia
Tatjana Šumanovac Ramljak ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička 54, 10000 Zagreb, Croatia
Kata Mlinarić-Majerski ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička 54, 10000 Zagreb, Croatia
Nikola Basarić   ORCID icon orcid.org/0000-0001-9412-9734 ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička 54, 10000 Zagreb, Croatia

Puni tekst: engleski, pdf (2 MB) str. 431-446 preuzimanja: 675* citiraj
APA 6th Edition
Sohora, M., Šumanovac Ramljak, T., Mlinarić-Majerski, K. i Basarić, N. (2014). Photodecarboxylation of N-Adamantyl- and N-Phenylphthalimide Dipeptide Derivatives. Croatica Chemica Acta, 87 (4), 431-446. https://doi.org/10.5562/cca2482
MLA 8th Edition
Sohora, Margareta, et al. "Photodecarboxylation of N-Adamantyl- and N-Phenylphthalimide Dipeptide Derivatives." Croatica Chemica Acta, vol. 87, br. 4, 2014, str. 431-446. https://doi.org/10.5562/cca2482. Citirano 22.09.2019.
Chicago 17th Edition
Sohora, Margareta, Tatjana Šumanovac Ramljak, Kata Mlinarić-Majerski i Nikola Basarić. "Photodecarboxylation of N-Adamantyl- and N-Phenylphthalimide Dipeptide Derivatives." Croatica Chemica Acta 87, br. 4 (2014): 431-446. https://doi.org/10.5562/cca2482
Harvard
Sohora, M., et al. (2014). 'Photodecarboxylation of N-Adamantyl- and N-Phenylphthalimide Dipeptide Derivatives', Croatica Chemica Acta, 87(4), str. 431-446. https://doi.org/10.5562/cca2482
Vancouver
Sohora M, Šumanovac Ramljak T, Mlinarić-Majerski K, Basarić N. Photodecarboxylation of N-Adamantyl- and N-Phenylphthalimide Dipeptide Derivatives. Croatica Chemica Acta [Internet]. 2014 [pristupljeno 22.09.2019.];87(4):431-446. https://doi.org/10.5562/cca2482
IEEE
M. Sohora, T. Šumanovac Ramljak, K. Mlinarić-Majerski i N. Basarić, "Photodecarboxylation of N-Adamantyl- and N-Phenylphthalimide Dipeptide Derivatives", Croatica Chemica Acta, vol.87, br. 4, str. 431-446, 2014. [Online]. https://doi.org/10.5562/cca2482

Sažetak
New dipeptide derivatives 1 and 3 were synthesized and their reactivity in the photochemical reaction of decarboxylation was investigated. The photodecarboxylation of N-adamantyl derivatives 1a and 1b and N-phenylphthalimide derivatives 3a and 3b probably takes place from the triplet excited state. The triplet excited state of 1a, 3a and 3b was characterized by laser flash photolysis. N-phenylphthalimides 3a and 3b undergo 2−5 times more efficient photodecarboxylation than N-adamantylphthalimides 1a and 1b. The aminoacid residue (Phe or Gly) at the C-terminus of the dipep-tide does not influence the photodecarboxylation efficiency. Product selectivity in the photoreactions is determined by the conformation of the molecules. N-phenylphthalimides with the separated elec-tron donor (carboxylate) and acceptor moiety (phthalimide) give only simple decarboxylation prod-ucts, whereas N-adamantyl derivatives also give cyclization products.

Ključne riječi
photodecarboxylation; dipeptides; phthalimides

Hrčak ID: 131545

URI
https://hrcak.srce.hr/131545

Posjeta: 870 *